Water → HCID 21746791, compound

HRID 1476360Notes

Reaction equation

HRID 1476360 reaction equation
[C:1]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=2)[CH:13]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].O.NN.O>C(O)COCCO>[CH2:1]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 867043802-Decanoyl-6-methoxynaphthalene

Product 1

HCID 21746791HCID 21746791, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

Under a nitrogen atmosphere, 2-decanoyl-6-methoxynaphthalene (9.4 g, 30 mmol) and potassium hydroxide (67 g, 1.2 mol) were dissolved in hydrazine monohydrate (70 ml, 1.4 mol) and diethylene glycol (200 ml). The solution was refluxed for 17 hours, and water (36 ml) was added. Under a stream of nitrogen, the solution was distilled to distill away an excessive amount of hydrazine and water. Further, the solution was refluxed under a nitrogen atmosphere for 41 hours. Subsequently, while using an ice bath, the solution was cooled by putting ice into the reaction solution, hydrochloric acid was slowly added until the solution became neutral. The reaction solution was extracted with ether (100 ml×3), and the obtained organic layer was washed with saturated saline water (100 ml×5). The organic layer was dried with anhydrous magnesium sulfate, and filtered. Then, the solvent was distilled away under reduced pressure. The obtained brown solid was recrystallized from hexane to obtain 6-decyl-2-hydroxynaphthalene (7.3 g, 90%) as a white solid.

Workup

  1. temperatureThe solution was refluxed for 17 hours
  2. distillationUnder a stream of nitrogen, the solution was distilled
  3. distillationto distill away an excessive amount of hydrazine and water
  4. temperatureFurther, the solution was refluxed under a nitrogen atmosphere for 41 hours
  5. temperaturethe solution was cooled
  6. additionwas slowly added until the solution
  7. extractionThe reaction solution was extracted with ether (100 ml×3)
  8. washthe obtained organic layer was washed with saturated saline water (100 ml×5)
  9. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThen, the solvent was distilled away under reduced pressure
  12. customThe obtained brown solid was recrystallized from hexane

Sources & evidence

ORD record
ord-0c6b393018fd43f4ba25873689a26b96
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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